Unexpected Staudinger reaction of α-azidophenylacetonitrile and triphenylphosphine: synthesis and crystal structure of aminotriphenylphosphonium salt of phenylmalononitrile
Abstract
Staudinger reaction of α-azidophenyiacetonitrile with triphenylphosphine in 1:2 molar ratio provides the triphenylphosphinazine derived from α-diazophenylacetonitrile, whereas in 2:1 molar ratio the final product is found to be the aminotriphenylphosphonium salt of phenylmalononitrile; X-ray structure analysis of this salt indicates that the anion and cation interact with one another via hydrogen bonding.